verubecestat   

GtoPdb Ligand ID: 8699

Synonyms: example 25 (US8940748) | MK-8931
Compound class: Synthetic organic
Comment: This is a new INN/USAN for a Merck BACE1 inhibitor for clinical trials in Alzheimer's disease (AD). Despite some early confusion surrounding the relationship between MK-8931, SCH 900931 and verubecestat, the article published by Scott et al. (2016) formally acknowledges verubecestat as MK-8931 [4].
Despite reaching Phase 3 clinical trial, Merck has announced (Feb 2017: Merck press release) termination of study NCT01739348 (in patients with mild-moderate AD) because they concluded there was no chance of achieving efficacy. This is the latest of a long list of BACE1 inhibitors to fail in AD. Papers reporting trial outcomes were published in May 2018 [1] and April 2019 [2].
2D Structure
Click here for structure editor
Physico-chemical Properties
Hydrogen bond acceptors 8
Hydrogen bond donors 2
Rotatable bonds 4
Topological polar surface area 126.13
Molecular weight 409.1
XLogP 1.84
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
Canonical SMILES Fc1ccc(nc1)C(=O)Nc1ccc(c(c1)C1(C)N=C(N)N(S(=O)(=O)C1)C)F
Isomeric SMILES Fc1ccc(nc1)C(=O)Nc1ccc(c(c1)[C@@]1(C)N=C(N)N(S(=O)(=O)C1)C)F
InChI InChI=1S/C17H17F2N5O3S/c1-17(9-28(26,27)24(2)16(20)23-17)12-7-11(4-5-13(12)19)22-15(25)14-6-3-10(18)8-21-14/h3-8H,9H2,1-2H3,(H2,20,23)(H,22,25)/t17-/m0/s1
InChI Key YHYKUSGACIYRML-KRWDZBQOSA-N
Classification
Compound class Synthetic organic
IUPAC Name
N-[3-[(5R)-3-amino-2,5-dimethyl-1,1-dioxo-6H-1,2,4-thiadiazin-5-yl]-4-fluorophenyl]-5-fluoropyridine-2-carboxamide
International Nonproprietary Names
INN number INN
10028 verubecestat
Synonyms
example 25 (US8940748) | MK-8931
Database Links
CAS Registry No. 1286770-55-5
ChEMBL Ligand CHEMBL3301601
GtoPdb PubChem SID 252166899
PubChem CID 51352361
RCSB PDB Ligand 66F
Search Google for chemical match using the InChIKey YHYKUSGACIYRML-KRWDZBQOSA-N
Search Google for chemicals with the same backbone YHYKUSGACIYRML
Search PubMed clinical trials verubecestat
Search PubMed titles verubecestat
Search PubMed titles/abstracts verubecestat
Search UniChem for chemical match using the InChIKey YHYKUSGACIYRML-KRWDZBQOSA-N
Search UniChem for chemicals with the same backbone YHYKUSGACIYRML